Last Updated on September 23, 2022 by Brian Drew

Boat shoes are a versatile kind of footwear that appeals to many people. They give out that young, youthful, and energetic vibe. They are not the formal kind of footwear that one wears to black tie events or formal occasions. The best boat shoes for sailing have a casual appeal and are hence used for casual activities.

But in recent years, due to their appealing looks, they are also being worn for semi-formal occasions, over slim-lined trousers and jeans. The traditional topsiders came in dark brown/ tan colors and navy colors, in leather.

But nowadays, they are being made from different materials and in different colors, to cater to the changing needs of people.

Ideally, these shoes are paired with polo shirts and chinos to get that casual look. However, it all depends on one’s tastes and dressing style. Anyone can create a trendy style and carry it off perfectly.

Here is a quick look at the best products in this category

Best boat shoe productsKey specificationsFull Review
Sebago Men’s DocksidesSizes available – Narrow, Medium, Wide and Extra wide. Colors available- Sand Suede, Black leather, Green, Whitewash, brown, navy, bright red, etc.

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Sperry Men’s Shoes Gold Cup A/O 2-EyeSizes available – Medium, Wide, Extra wide. Colors available – Brown, tan, navy, black, Dark tan, red, etc.

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Sperry Top-Sider Men’s Billfish Slip OnSizes available – Medium width from sizes 8 to 13 Colors available – Coffee tan and beige
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Timberland Men’s Classic Two-EyeSizes available – size 6 to size 15 Color available – light brown, brown, burnished tan, navy, dark brown, root beer brown.Read Here
Helly Hansen Men’s TrysailSizes available- Size 7 to 11.5 Colors available – Ebony, Light gray, gray, Navy.Read Here

Most comfortable boat shoes | Sebago Men’s Docksides Boat Shoe

Best Boat Shoes for Sailing

The Sebago brand is a timeless brand that is known for its original and genuine designs. Made with a durable traction sole, these topsiders are simply one of the best boat shoes for sailing available on the market. The range of colors in which the deck shoes are available is astonishing.

The Sebago Men’s Docksides Boat Shoes are crafted in leather and not canvas. These are made to deliver the best performance and give you the utmost comfort. You can wear them on the boats or wear them while walking on the streets, the Sebago Docksides are a must-have for the urban male.

The design is classic and therein lies its appeal.

The features of this boat shoe are summarized below:

  • Made of imported leather.
  • Laces are provided for that extra support in rough conditions.
  • A full rubber sole with a classic wavy pattern.
  • The rubber sole is non-marking.
  • It features moc-toe stitching.
  • There is a molded EVA foam insole too.


  • The leather quality is really good.
  • Very comfortable, even without socks.
  • Durable and long-lasting.
  • The foam insole makes it very comfortable for day-long wear.
  • Available in different width sizes.


  • Due to the different width sizes available, finding the right fit often becomes cumbersome. Sometimes the sizes are too large or too small.
  • Takes time to break in.

best boat shoes for sailing – Sperry Men’s Shoes Gold Cup A/O 2-Eye Boat Shoe

A classic and stylish accessory, the Sperry Men’s Gold Cup A/O 2-Eye shoes are considered top-notch shoes for sailing. The features and the designs of these deck shoes are superior and crafted to perfection.

Made from the finest leathers, these deck shoes have minute attention to detail. The leather is premium and offers a good comfort factor. The 360-degree lacing system ensures a snug and secure fit. The gold-plated eyelets that come with this pair give it some pizzazz.

Some of its outstanding features are highlighted herein:

  • Made from the finest quality, imported leather.
  • Handsome detailing.
  • Good quality gold-plated eyelets that are made from anon-corrosive material.
  • 360-degree lacing system.
  • Stain-resistant and water-resistant leather.
  • It has memory foam footbeds for added comfort.
  • Has a lambskin inner lining for that soft feeling inside the shoes.
  • The rubber outsole is non-marking.
  • Extra cushions in the midsole.


  • Good quality of construction.
  • Excellent durability
  • Exceptionally comfortable.
  • Can be worn with or without socks.
  • Easy to slip on and slip off the shoes.
  • The lacing system ensures a snug fit.
  • Memory foam footbeds and extra midsole cushions provide extreme comfort.
  • They dry up nicely without any stiffness.


  • A little expensive.
  • A few people experience more time to break in and hence the shoes have a tendency to pinch.

Best boat shoes for walking | Sperry Top-Sider Men’s Billfish Slip On

Stylishly contoured these deck shoes are the best shoes for walking. Perfect for any other activities too, these are slip resistant with a molded rubber sole. They have water channeling grooves which make them ideal for all your maritime activities.

The leather uppers are also specially treated and oil tanned. There are nylon mesh quarter panels that add to the breathability factors.

This piece of footwear is extremely durable and ideal for everyday casual wear. They also come with a shock-absorbing EVA heel cup that gives added comfort.

Some of the features are:

  • Made of imported leather.
  • Hand-sewn with moc construction.
  • Molded rubber outsole which is slip resistant.
  • Nylon meshes quarter panels.
  • Stain-resistant leather uppers.
  • Have shock-absorbing EVA heel cups.
  • They also have molded EVA cushion midsole.


  • Great appearance and comfort.
  • Made from high-quality materials.
  • Highly durable.
  • Perfect for leisure boating.


  • These are mostly meant to be worn without socks. There is a tendency for them to be tight if worn with socks.
  • It takes some time to break in.
  • Getting the right fit and size may be an issue. As the leather tends to stretch after some usage, the shoes may feel tight or loose at times.

Timberland Men’s Classic Two-Eye Boat Shoe

Timberland’s deck shoes are more of a classic and traditional variety. Mostly available in the dark colors of brown and navy, they have all the comforts of a deck shoe.

Timberland’s Men’s Classic 2-Eye boat shoe certainly gives you that overall-nautical-inspired look and feel. The entire construction of the shoes simply reminds you of everything associated with water. The rubber outsoles have great grip and maximum traction.

After all, deck shoes should have good grip and traction, for which they are famous. The leather upper is made of premium leather and is hand sewn.

Quite ruggedly casual, these are good for boating as well as for walking. Some of the excellent features of this product are mentioned here:

  • They are made from premium quality leather.
  • They have the moccasin toe construction.
  • A slotted collar with rawhide lacing is another good feature.
  • There is an EVA insert with foam, adding more comfort.
  • Non-marking rubber outsole with siping/wave patterns.
  • Corrosion-resistant hardware is used for increased longevity around water.


  • The rawhide lace makes for a customized fit.
  • Easy to slip on and off.
  • Give a handsome two-tone look.
  • Most of the metals are corrosion-resistant.
  • Very comfortable to wear.


  • They have a half insole, which can be fixed.
  • These shoes have to be worn with socks. Otherwise, the insides get really uncomfortable, due to the half insoles.

Best boat shoes for fishing | Helly Hansen Men’s Trysail Boat Shoe

This is a nice product, good as a boat shoe for fishing. These deck shoes are high-quality protective gear, meant for work and sport.

The construction of the deck shoes is really outstanding and good with really great features incorporated into them. They have a combination of mesh and synthetic construction for super comfort and breathability. The midsole is an EVA midsole. The flexible outer rubber sole provides good traction on slippery surfaces.

The Helly HansenTrysail deck shoes are the perfect accessory for those seaside adventures and beach trips.

A few great features of this product are outlined here:

  • Imported leather construction.
  • Have a synthetic and mesh upper.
  • The midsole is decoupled EVA midsole.
  • The outsole is made of flexible rubber.
  • Has a quick dry mesh giving more comfort.


  • They are quite easy on the feet.
  • Very comfortable.
  • They are cool and not stuffy inside.
  • Can be used in water all day long, with superior comfort.
  • The outsole is engineered in such a way as to give exceptional grip.
  • Highly durable.


  • Not available in a wide range of colors.
  • The pop color lacing may not be a preference for many.


The deck shoes though originally invented for practical utilitarian purposes have found a great place in the wardrobes of men. Because of their versatile nature, they are also worn for semi-formal occasions.

A review of the best boat shoes for sailing shows us that there are many deck shoes that are being made to give extra comfort and also add on that extra detailing, to make them perfect for the occasion.

The Sebago Men’s Docksides and the Sperry Men’s Shoes Gold Cup A/O 2-Eye deck shoes are really great with awesome features. If you want some really stylish range then the Sperry Men’s Shoes Gold Cup range of deck shoes should be your choice. They have a nice range of topsiders in various colors.

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